The success of Benitez's reign at Liverpool has been intrinsically linked to the fortunes of his side in meetings with Chelsea - and their clash in this season's Champions League semi-final should prove no different. In 2005, he joined Liverpool's most successful manager - Bob Paisley - and Jose Mourinho as the only men to win the UEFA Cup and European Cup in successive seasons, when he took the Reds to glory in his first season at Anfield after leading Valencia to the lesser trophy in 2004.
A year later he won the FA Cup in equally dramatic circumstances, helped by Steven Gerrard's injury-time equaliser against West Ham, and in 2007 took Liverpool to the Champions League final again where they lost 2-1 to AC Milan. Benitez was a talented young midfielder with Real Madrid's youth sides, but injury saw him move into coaching with Real Madrid B in 1986.
After spells at various Spanish clubs including Real Valladolid, Osasuna and Tenerife, he moved to Valencia in 2001. While at the Mestalla he won the club's first title for three decades in 2002. In 2004 Valencia won La Liga for the second time in three seasons, and also beat Marseille to win UEFA Cup. And behind his success in cup competition with Liverpool is his ability to deliver against the team from west London, particularly in semi-finals.
In 2005 his Liverpool side avenged defeat in the League Cup final by winning a highly-charged Champions League semi-final with a disputed Luis Garcia goal. The following season Liverpool halted Chelsea's FA Cup challenge with another semi-final victory at Old Trafford .
And in 2007 Benitez completed a hat-trick of semi-final victories over Chelsea after Liverpool claimed a penalty shootout win to take their place in a second European Cup final in three seasons.
Chelsea manager Avram Grant, like Benitez, spent his early years studying tactics and formations and had a far from glittering playing career. In 1974 he became youth coach at Hapoel Petah Tikva at the young age of 19, and became the youngest ever manager in the Israeli top flight when he took charge of the first team in 1986.
Grant enjoyed domestic success with Maccabi Tel Aviv and Maccabi Haifa where he won two league titles with each and then was in charge of the latter when they became the first ever Israeli side in the Champions League. He took charge of the Israel national team in 2002 but missed out in qualification for Euro 2004 and narrowly missed a spot at the 2006 World Cup.
The 52-year-old has subsequently led Chelsea to the League Cup final, where they lost to Tottenham in extra-time. Chelsea do still have an outside chance of winning the Premier League although Grant showed signs of the pressure mounting in a bizarre post-match press conference after his side's 1-0 win over Everton at Goodison Park.
Realistically the Champions League remains the Israeli's best hope of silverware, and would probably save him from the ire of the Shed End as well as the axe of owner Roman Abramovich. Grant has locked horns with Benitez twice since taking over from 'The Special One' and his record reads won one, drawn one. In his first meeting with the Spaniard he steered Chelsea to a 2-0 home victory in the Carling Cup quarter-finals thanks to goals from Frank Lampard and Andriy Shevchenko followed by February's goalless draw in west London in the Premier League.
What Grant's meeting with Benitez in Europe may lack in entertainment, it will be more than compensated for by the drama with the stakes so high for both managers.
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